2-{2-[(2E,3aS,4S,5R,6aS)-5-hydroxy-4-[(3S,4S)-3-hydroxy-4-methylnona-1,6-diyn-1-yl]-octahydropentalen-2-ylidene]ethoxy}acetic acid

• ChemBase ID: 164750
• Molecular Formular: C22H30O5
• Molecular Mass: 374.4706
• Monoisotopic Mass: 374.20932406
• SMILES: [C@@H]1([C@@H](C[C@H]2[C@@H]1C/C(=C/COCC(=O)O)/C2)O)C#C[C@H]([C@H](CC#CCC)C)O
• Canonical SMILES: CCC#CC[C@@H]([C@@H](C#C[C@H]1[C@H](O)C[C@H]2[C@@H]1C/C(=C/COCC(=O)O)/C2)O)C
• InChI: InChI=1S/C22H30O5/c1-3-4-5-6-15(2)20(23)8-7-18-19-12-16(9-10-27-14-22(25)26)11-17(19)13-21(18)24/h9,15,17-21,23-24H,3,6,10-14H2,1-2H3,(H,25,26)/b16-9+/t15-,17-,18+,19-,20+,21+/m0/s1
• InChIKey: ARUGKOZUKWAXDS-SEWALLKFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-[(2E,3aS,4S,5R,6aS)-5-hydroxy-4-[(3S,4S)-3-hydroxy-4-methylnona-1,6-diyn-1-yl]-octahydropentalen-2-ylidene]ethoxy}acetic acid
• IUPAC Traditional name: {2-[(2E,3aS,4S,5R,6aS)-5-hydroxy-4-[(3S,4S)-3-hydroxy-4-methylnona-1,6-diyn-1-yl]-hexahydro-1H-pentalen-2-ylidene]ethoxy}acetic acid
• Synonyms: 2-[2-[(2E,3aS,4S,5R,6aS)-Hexahydro-5-hydroxy-4-[(3S,4S)-3-hydroxy-4-methyl-1,6-nonadiyn-1-yl]-2(1H)-pentalenylidene]ethoxy]acetic Acid; ZK 96480; Cicaprost

Database IDs

• CAS Number: 94079-80-8
• PubChem SID: 162258885
• PubChem CID: 5311044

CALCULATED PROPERTIES

• Lipinski's Rule of Five: true
• Acid pKa: 3.9525373
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.2273479
• LogD (pH = 7.4): -0.40320867
• Log P: 2.78245
• Molar Refractivity: 105.1701 cm^3
• Polarizability: 39.81792 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 10

DETAILS

Toronto Research Chemicals - C432750

A highly potent anti-metastatic Prostacyclin (P839060) analogue.

REFERENCES

• McFadden, E., et al.: Lancet, 364, 1519 (2004)
• Stewart, S., et al.: J. Biol. Chem., 279, 29109 (2004)
• Bundey, R., et al.: Mol .Pharmacol., 70, 1700 (2004)